Stannous chloride dihydrate → 4-Trifluoromethyl-1,2-phenylenediamine

HRID 1671847Notes

Reaction equation

HRID 1671847 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[NH2:14])([O-])=O.O.O.[Sn](Cl)Cl>C(O)C>[F:11][C:10]([F:12])([F:13])[C:8]1[CH:9]=[C:4]([NH2:1])[C:5]([NH2:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 67865Benzenamine, 2-nitro-4-(trifluoromethyl)-

Product 1

HCID 5208224-Trifluoromethyl-1,2-phenylenediamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Nitro-4-trifluoromethyl-phenylamine was purchased from Aldrich. It was reduced with tin (11) chloride dihydrate in ethanol to give 4-trifluoromethyl-benzene-1,2-diamine (Scheme 3). The diamine was reacted with hexaketocyclohexane octahydrate to give [(HATNA)(CF3)3]. The product contains two isomers (from HPLC). The product is a yellow solid. It is soluble in common organic solvent including dichloromethane, THF and hot methanol. It was purified by flash chromatography on silica gel eluting with dichloromethane.

Sources & evidence

ORD record
ord-4b1f9edc671e431ebb5aa0e2e6da2c85
Source dataset
uspto-grants-2011_08
Patent number
US07994423B2

Reaction notes

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